Phlegmacaritones A and B, a Pair of Serratane-Related Triterpenoid Epimers with an Unprecedented Carbon Skeleton from Phlegmariurus carinatus .

A pair of novel serratane-related triterpenoid epimers, phlegmacaritones A ( 1 ) and B ( 2 ), possessing an unprecedented 15,30-lactone-14,15-seco skeleton, six new serratane-type triterpenoids, phlegmanols G-L ( 3 - 5 and 14 - 16 ), and 16 known compounds were isolated from the whole plant of Phlegmariurus carinatus . The structures of the new metabolites were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism calculations. A possible biosynthetic pathway for phlegmacaritones A ( 1 ) and B ( 2 ) was proposed. All compounds were submitted to cytological profiling on a cell line derived from a patient with Parkinson's disease. Phlegmacaritone B ( 2 ) induced a distinct phenotypic profile with alterations in α-tubulin, mitochondria, and autophagosomal and early endosomal features.